Siesta Key, FL Homes

/54
$995,000
- 1 Bed
- 1 Bath
- 928 Sq Ft
5400 Ocean Blvd Unit 9-4, Sarasota, FL 34242

Discover coastal luxury at Beach Terrace, one of Siesta Key's most coveted addresses. Perfectly positioned at the end of the village with direct Gulf of Mexico frontage, this exceptional 1 bedroom, 1 bathroom corner residence offers an unparalleled beachfront lifestyle with breathtaking panoramic views that truly set it apart. This thoughtfully designed condominium showcases sweeping vistas that

Mickey Kiernan MICHAEL SAUNDERS & COMPANY

5400 Ocean Blvd Unit 9-4, Sarasota, FL 34242
/26
$7,400 per month
- 4 Beds
- 3 Baths
- 2,248 Sq Ft
- House for Rent
5153 Sandy Cove Ave, Sarasota, FL 34242

You will Never Want to Leave this 4-bedroom house on Siesta Key! Mid-Century Modern, 4 bedroom home with saltwater, heated Pool with canal views. Located within a 6 minute bike ride to Siesta Key's Beach Access #5 and walking distance to everything that Siesta Key Village has to offer. This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, "Sarasota School of Architecture style"

Kelly Anderson RE/MAX ALLIANCE GROUP

5153 Sandy Cove Ave, Sarasota, FL 34242
/2
$446,000 Sold Sep 01, 2025
- 1,012 Sq Ft
- $441/SF
- 92 Days On Market
- 2 Beds
- 2 Baths
- Built 1975
5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

This unit did not flood in any storms! Seller offering a 1 point rate buydown! Experience the ultimate in coastal living from this beautifully updated condo located just steps from the world-renowned Siesta Key Beach. Situated in a sought-after Siesta Key community, this ground floor residence offers abundant natural light and a relaxed Florida lifestyle. The spacious 2-bedroom, 2-bath layout

Thomas Cail RE/MAX ALLIANCE GROUP

5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

/30
Est $557,123 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 872 Sq Ft
5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

/88
$799,900
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
1125 W Peppertree Dr Unit 706, Sarasota, FL 34242

LOCATION, LOCATION, LOCATION! Discover your slice of paradise in the desirable Peppertree Bay community on Siesta Key. This fabulous, turnkey furnished 7th-floor Gulfside condo, offers direct beach access and panoramic views of Siesta Key and Downtown Sarasota. Featuring tile flooring throughout, this 2-bed, 2-bath layout includes a custom kitchen with quartz countertops, mosaic tile backsplash,

Christine Green COLDWELL BANKER REALTY

1125 W Peppertree Dr Unit 706, Sarasota, FL 34242
/30
$3,500 per month
- 2 Beds
- 2 Baths
- 991 Sq Ft
- Condo for Rent
1215 S Portofino Dr Unit 308, Sarasota, FL 34242

BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available Fall 2025 — and May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed

Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

1215 S Portofino Dr Unit 308, Sarasota, FL 34242
/2
$900,000 Sold Aug 29, 2025
- 1,767 Sq Ft
- $509/SF
- 57 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1968
5108 Saint Albans Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer | BEACH VIBES? Check, PRIME LOCATION? Check, HIGH END RENOVATIONS all completed in 2025? Check, check & check! Welcome to the ultimate in Florida living – whether you are looking to settle in full time or score an amazing SHORT TERM RENTAL/VACATION HOME, this one is a MUST SEE! Located in the

Jennifer Wemert WEMERT GROUP REALTY LLC

5108 Saint Albans Ave, Sarasota, FL 34242

/53
Est $599,665 Not Listed For Sale
- 2 Beds
- 2 Baths
- 975 Sq Ft
1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

/78
$2,495,000
- 4 Beds
- 3.5 Baths
- 2,757 Sq Ft
3959 Somerset Dr, Sarasota, FL 34242

Boaters, this one is rare! On deep, protected water in Cocoanut Bayou with no fixed bridges. This fully remodeled home on Siesta Key’s north end includes a deeded dock with water, electric and a 20,000-pound lift—holds up to a 40-foot boat—with fast access to Sarasota Bay and the Gulf in under 10 minutes. Inside and out, this free-standing four-bedroom, 3.5-bath home has been thoughtfully

Peter Mason PREMIER SOTHEBY'S INTERNATIONAL REALTY

3959 Somerset Dr, Sarasota, FL 34242
/17
$15,000 per month
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
- House for Rent
339 Avenida de Paradisio, Sarasota, FL 34242

scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!

Valerie McInerney LPT REALTY, LLC

339 Avenida de Paradisio, Sarasota, FL 34242
/2
$1,200,000 Sold Aug 29, 2025
- 1,337 Sq Ft
- $898/SF
- 180 Days On Market
- 2 Beds
- 2 Baths
- Built 1986
5740 Midnight Pass Rd Unit 402, Sarasota, FL 34242

The Gulf & Bay Club on Siesta Key is, by its own definition: exclusive, elegant and engaging. A gated 32-acre community with unrivaled waterfrontage and amenities, this is not your typical beach front condo, this is unparalleled resort living on Siesta Key. In this premium community, building F is ostensibly the prime location with sprawling views of the white sands of Crescent beach that gently

Rudy Dudon MICHAEL SAUNDERS & COMPANY

5740 Midnight Pass Rd Unit 402, Sarasota, FL 34242

/36
Est $726,426 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,270 Sq Ft
5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

/71
$699,900 Open Sat 12PM - 2PM
- 2 Beds
- 2 Baths
- 940 Sq Ft
925 Beach Rd Unit 112, Sarasota, FL 34242

Endless vacations await at La Siesta! This highly desirable first-floor, recently remodeled two-bedroom, two-bath corner condominium has been beautifully updated throughout, including a modern new kitchen, stylish finishes, and tasteful décor. The open layout and all-tile flooring make the space bright and inviting for both relaxation and entertaining. Step out to your private screened lanai and

Stuart Francis EXP REALTY LLC

925 Beach Rd Unit 112, Sarasota, FL 34242
/36
$2,300 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1350 N Portofino Dr Unit 207, Sarasota, FL 34242

This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1350 N Portofino Dr Unit 207, Sarasota, FL 34242
/2
$600,000 Sold Aug 29, 2025
- 978 Sq Ft
- $613/SF
- 191 Days On Market
- 2 Beds
- 2 Baths
- Built 1962
4522 Banan Place, Sarasota, FL 34242

Existing home has been mitigated for water damage. One of the best values on Siesta Key. Photos of the existing home are prior to the 2024 storm damage. Large lot at over 10,880 SF Right by Out of Door Academy and walking distance to beach and Siesta Village. Attention Veterans! It may be possible for qualifying veterans to assume a huge part of the purchase price in the form of a 2.85% VA

Michelle Shiver KELLER WILLIAMS ON THE WATER S

4522 Banan Place, Sarasota, FL 34242

/33
Est $649,977 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5963 Midnight Pass Rd Unit 339, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 339, Sarasota, FL 34242

/75
$975,000
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
6140 Midnight Pass Rd Unit 902, Sarasota, FL 34242

Your Dream Beach Escape Awaits on Siesta Key!Tired of long winters or hectic city life? Discover the ultimate retreat in this luxurious 9th-floor penthouse overlooking Siesta Key’s world-renowned Crescent Beach. With uninterrupted Gulf views, you’ll enjoy breathtaking sunsets and the soothing sounds of the surf each day.This spacious 1-bedroom, 1-bath unit features a sleek open floorplan

Suki Scollo COLDWELL BANKER REALTY

6140 Midnight Pass Rd Unit 902, Sarasota, FL 34242
/40
$11,000 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242

Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach

Andy Moore GULF COAST REALTY & MANAGEMENT

1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
/2
$630,000 Sold Aug 29, 2025
- 1,296 Sq Ft
- $486/SF
- 240 Days On Market
- 2 Beds
- 2 Baths
- Built 1951
633 Calle de Peru, Sarasota, FL 34242

New build or restoration opportunity!! This unique two-bedroom, two bathroom, three car garage bungalow is nestled in the heart of Siesta Key. Located minutes away from, world famous Siesta Key beach and the village; it is perfectly situated to live the island life. Unfortunately, the house was flooded during Helene and has been stripped down and is ready for its new owners. Remodel the house

Bradley Kayser COLDWELL BANKER REALTY

633 Calle de Peru, Sarasota, FL 34242

/49
Est $642,249 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 975 Sq Ft
1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

/42
$899,000
- 2 Beds
- 2 Baths
- 1,217 Sq Ft
1269 Dockside Place Unit 115, Sarasota, FL 34242

This spacious condo has easy access to Siesta Key Beach and a DEEDED 25-FOOT BOAT SLIP WITH A LIFT!! There is water and electric to the dock. Yes, this is a rare opportunity to have both your boat and a nearby world-famous beach in a nicely laid out two-bedroom, two-bath turnkey furnished condo. The master bedroom has views of the harbor while the guest room has a peaceful garden view. This condo

Mina Johnson MICHAEL SAUNDERS & COMPANY

1269 Dockside Place Unit 115, Sarasota, FL 34242
/80
$8,500 per month
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- House for Rent
5216 Calle de Costa Rica, Sarasota, FL 34242

Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely

Beth Dilley ASCENDIA REAL ESTATE

5216 Calle de Costa Rica, Sarasota, FL 34242
/2
$1,150,000 Sold Aug 28, 2025
- 1,335 Sq Ft
- $861/SF
- 12 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
5790 Midnight Pass Rd Unit 702, Sarasota, FL 34242

Gulf-front living at its finest in the exclusive Gulf & Bay Club on Siesta Key! This updated 2BD/2BA condo offers breathtaking, unobstructed views of the Gulf and Siesta Key Beach with their stunning nightly sunsets. The open layout features a modern kitchen with granite counters and white contemporary cabinetry. A spacious living/dining area that opens to a private beachfront balcony. The

Maurice Menager MICHAEL SAUNDERS & COMPANY

5790 Midnight Pass Rd Unit 702, Sarasota, FL 34242

/41
Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,463 Sq Ft
5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

/18
$700,000
- 2 Beds
- 3 Baths
- 988 Sq Ft
5950 Midnight Pass Rd Unit 311, Sarasota, FL 34242

Siesta Beach House – Unit 311 / Beach CoveDiscover the perfect blend of coastal charm and modern comfort with this rarely available 2-bedroom, 3-bath townhome-style condo in the desirable Siesta Beach House community. Located just steps from world-renowned Siesta Key Beach and only minutes from the dining, shopping, and nightlife of Siesta Key Village, this home offers the best of island

Brad Wilson M&M PROPERTY MANAGEMENT GROUP

5950 Midnight Pass Rd Unit 311, Sarasota, FL 34242
/58
$8,000 per month
- 3 Beds
- 2 Baths
- 2,002 Sq Ft
- House for Rent
5640 Cape Leyte Dr, Sarasota, FL 34242

It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

Beth Dilley ASCENDIA REAL ESTATE

5640 Cape Leyte Dr, Sarasota, FL 34242
/2
$920,000 Sold Aug 28, 2025
- 3,362 Sq Ft
- $274/SF
- 144 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1983
614 Tropical Cir, Sarasota, FL 34242

Lovingly owned for 20 years, this tropical retreat offers privacy, charm, and thoughtful updates throughout. Recent enhancements include lush Areca palms for a private, resort-style setting, and an expanded pool area complete with a cozy seating space, large umbrella, and fire pit-perfect for relaxing or entertaining under the stars. Nestled in the heart of Siesta Key, and close to one of the

Stacy Liljeberg MICHAEL SAUNDERS & COMPANY

614 Tropical Cir, Sarasota, FL 34242

/38
Est $621,747 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

/40
$965,000
- 2 Beds
- 2 Baths
- 1,760 Sq Ft
1161 Coquille St Unit 206, Sarasota, FL 34242

Welcome to coastal elegance and a rare opportunity to own one of only 27 townhomes in the highly sought-after Coquille community, nestled on the picturesque barrier island of Siesta Key, where you are steps to having your feet in the famous soft, white quartz sand that makes Siesta Beach famous. This spacious and light-filled, furnished 2-bedroom, 2-bathroom residence also includes a Florida

Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

1161 Coquille St Unit 206, Sarasota, FL 34242
/41
$5,000 per month
- 2 Beds
- 2 Baths
- 1,424 Sq Ft
- House for Rent
5577 Contento Dr, Sarasota, FL 34242

This is a short term rental. Listing reflects off season rate. Available peak season month: January 3rd - 31st, 2026. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously

Beth Dilley ASCENDIA REAL ESTATE

5577 Contento Dr, Sarasota, FL 34242
/2
$590,000 Sold Aug 28, 2025
- 753 Sq Ft
- $784/SF
- 178 Days On Market
- 2 Beds
- 1 Bath
- Built 1972
901 Beach Rd Unit 402, Sarasota, FL 34242

Siesta Key Beachfront Paradise – Rare Top-Floor Gulf View Condo!Location, location, location! This stunning 2-bedroom, 1-bathroom, 753 sq. ft. top-floor unit in La Siesta’s Building A offers unobstructed, direct Gulf views from both the private screened balcony and the spacious primary bedroom. Rarely available and highly sought after, this turn-key furnished condo is situated directly across

Jane Ebury COMPASS FLORIDA LLC

901 Beach Rd Unit 402, Sarasota, FL 34242

/31
Est $526,701 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 900 Sq Ft
1110 S Moonmist Ct Unit M-11, Sarasota, FL 34242

1110 S Moonmist Ct Unit M-11, Sarasota, FL 34242

/29
$825,000
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
19 Whispering Sands Dr Unit 203, Sarasota, FL 34242

Opportunity Awaits with a Million-Dollar View! Imagine starting with a blank canvas and creating your very own slice of paradise—complete with private beach access and unobstructed Gulf views. Welcome to this light-filled 2 bed / 2 bath residence in the coveted North Tower of Whispering Sands, a premier 55+ Gulf-front community. Perfectly perched on the 2nd floor, this home captures sweeping

Steve Abbe COLDWELL BANKER REALTY

19 Whispering Sands Dr Unit 203, Sarasota, FL 34242
/64
$2,450 per month
- 2 Beds
- 1 Bath
- 680 Sq Ft
- Condo for Rent
446 Canal Rd Unit 5, Sarasota, FL 34242

This is a short term rental. Listing reflects peak season weekly rate. Discover Key Lime Retreat, an end-unit condo perfectly situated in the heart of Siesta Key. This delightful getaway combines comfort with modern style, ideal for families or a group of friends. Tucked away in a tropical garden setting, you'll enjoy access to a community pool, perfect for a refreshing dip. Everything you need

Beth Dilley ASCENDIA REAL ESTATE

446 Canal Rd Unit 5, Sarasota, FL 34242
/2
$700,000 Sold Aug 27, 2025
- 1,280 Sq Ft
- $547/SF
- 155 Days On Market
- 2 Beds
- 2 Baths
- Built 1988
1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242

Here is your opportunity for a Gulf and Bay Bayside 2nd-floor walk-up Condo. Oh so lovely views of the pond and the water fountain, Weekly rental makes this an excellent investment. Just a short walk and you are on our famous Siesta Key Beach along with this deeded beach access there are wonderful amenities. - Two heated pools, clubhouse, BBQ area, fishing pier, pickleball and tennis courts,

Fred Sieger Jr COMPASS FLORIDA LLC

1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242

/47
Est $701,042 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
1101 Lake House Cir Unit C-206, Sarasota, FL 34242

1101 Lake House Cir Unit C-206, Sarasota, FL 34242

/99
$739,000
- 1 Bed
- 1 Bath
- 816 Sq Ft
797 Beach Rd Unit 509, Sarasota, FL 34242

PENTHOUSE" OPPORTUNITY on the 5th Floor of Building 797 in Sought After & Gated CRESCENT ROYALE! As you walk through the door you will be astounded with the beautiful views of the Gulf of Mexico & Siesta Beach! Own your own piece of Siesta Key and enjoy the gorgeous nightly sunsets on the top floor. This updated unit has been well maintained and tastefully furnished, updated with a functional

Sandy Gamble Hulvat WATERSIDE REALTY LLC

797 Beach Rd Unit 509, Sarasota, FL 34242
/25
$6,500 per month
- 1 Bed
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242

Heaven on Siesta Key, in perfect condition, up to date, and simply beautiful. This spacious, first floor one bedroom with a bay/harbor water view from your lanai is immaculate, beautifully decorated and offers every comfort for your favorite vacation stay. The modern kitchen shines with new cabinets, lighting, paint, and kitchen work desk. Elegant bathroom with new walk in shower featuring

Andy Moore GULF COAST REALTY & MANAGEMENT

1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
/2
$629,900 Sold Aug 25, 2025
- 753 Sq Ft
- $837/SF
- 22 Days On Market
- 2 Beds
- 1 Bath
- Built 1972
925 Beach Rd Unit 408, Sarasota, FL 34242

Rare Turnkey "PENTHOUSE OPPORTUNITY" located in one of the front buildings with a Full Gulf View directly across from the world-famous #1 rated Siesta Key Beach with beautiful quartz crystal sand! The exceptional office staff make this community well managed & this unit has a proven track record of 57K gross rental income in '2023 & 53K for '2024 & year-to-date in '25 (Jan-June) 37K which can be

Debbie Hering DEBBIE HERING REALTY & ASSOC.

925 Beach Rd Unit 408, Sarasota, FL 34242

/6
Not Listed For Sale
0 Venice Ln Unit 4,5, Sarasota, FL 34242

0 Venice Ln Unit 4,5, Sarasota, FL 34242

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